Here's the 'clear as mud' version.
-Plebes are allowed one pass per semester. They can earn more passes (For ex, my DS's Beast company was Best Company during Beast {based on points} and they earned an extra pass).
- Passes are privileges- not entitlements. They are not guaranteed, they must be applied for, the TAC must approve it, and to be approved the cadet must be in good standing academically, physically (passed the APFT to the West Point standard), and militarily (discipline.) They will most likely not secure a final approval until the week before the pass weekend so making travel arrangements involving flight bookings is a bit risky.
- to be picky, a pass is not leave. Leave is what every cadet gets like Thanksgiving and Christmas. However, if you are not in good standing academically, physically and militarily, you not may not be granted leave. Case in point, Spring Break followed Plebe Parent Weekend this year. When we were leaving West Point with our Plebe after PPW was over, we saw about a dozen cadets picking up trash. Seems they had some areas where they were not in good standing and therefore, there was not going to be a Spring Break for them, at least away from West Point.
- So yes, they can use their one pass for Labor Day IF they are in good standing academically, physically and militarily and if their TAC approves. The approval MAY not come until a day or two before Labor Day. BUT, who knows, West Point may decide to not allow passes for Labor Day this year for whatever reason.
The only thing that is certain is that nothing is certain.
Welcome to West Point and the military!